“The clientele is a little more conservative in general,” said Ms. Charles, 39, comparing the tony Montague-area shoppers to those along trendy Fifth Avenue in Park Slope, where her other stores, Razor and Serene Rose, are located.

But rather than expand her locally designed apparel business to equally hip Smith Street in Carroll Gardens—which already offers a number of chic clothing shops not entirely unlike Blue Rose—Ms. Charles chose to stand out as a sort of “pioneer” along staid Montague Street. “We bring a little bit of the funky element to the strip,” she said.

It’s about time somebody brought the funk. This stuffy nabe could use some of whatever Smith or Fifth is selling.

ONCE REGARDED AS THE BOROUGH’S PREMIER commercial corridor, Montague Street just doesn’t carry the same cachet, amid the retail resurgence taking place south of Atlantic Avenue.

“I don’t just hear that the street’s lost cachet—I’ve heard people say there’s nothing to buy and they don’t go there anymore,” said Judy Stanton, executive director of the Brooklyn Heights Association. “The shops on Court Street are a lot more interesting. There’s more variety; there are smaller boutiques. They’re the kind of shops the residents here would say they’d like.”

A historic nesting ground for the families of well-to-do Wall Street types dating back to the 18th century, Brooklyn Heights has long claimed dibs as “America’s First Suburb.” But it might as well be any ol’ suburb in America, with so many of the same chains you see everywhere else taking up precious space along Montague Street’s four short blocks.

Even so, Montague Street remains the gold standard when it comes to Brooklyn retail—at least on paper. According to the latest figures from Massey Knakal Realty Services, shopkeepers and restaurateurs on Montague Street pay the highest retail rents, with rates upward of $100 to $134 per square foot on average, compared to $50 to $74 a square foot on trendy Smith Street and Fifth Avenue.

Of course, prestige from a realtor’s perspective is one thing; from a consumer’s point of view, things can look a lot different. As Smith and Fifth continue to add eclectic new shops and restaurants, boosting their surrounding neighborhoods’ desirability, Montague Street is rapidly losing what few charms it has left. Goodbye, Mr. Souvlaki, after 33 wonderful years of seasoned meat on a stick; hello, Sprint PCS.

If not for the iconic promenade overlooking the East River at Montague Street’s westernmost end, the average visitor strolling past Chipotle, Banana Republic, Häagen-Dazs, Nine West and Starbucks wouldn’t know these hallowed Heights from, say, Shaker Heights, Ohio.

The Middle America comparison is perhaps most noticeable at night, when foot traffic on Montague all but disappears. The scores of nearby Borough Hall–area office workers, college students and occasional tourists who prowl the street during the daytime, seeking lunch or perhaps the latest eyeliner from MAC cosmetics, presumably have less boring places to spend their evenings.

Even on the relatively warm Saturday night of March 10, when diners packed many of nearby Smith Street’s eclectic eateries, the less fashionable joints on Montague offered plenty of empty tables. After 10 p.m., as Smith Street’s youthful masses barhopped among its hotspots, Montague’s more mature (yet far less numerous) loiterers merely window-shopped, browsing the posted real-estate listings among the many brokerage offices lining its four blocks.

It’s a far cry from the café-lined strip with “revolution in the air” that Bob Dylan described in his 1974 tune “Tangled Up in Blue.”

If places like Smith Street and Fifth Avenue are presently experiencing a sort of nightlife renaissance, then Montague Street has clearly hit a recession.

“I’m here till we close at 9 most Saturday nights, and it’s pretty quiet by then,” said Bill, a manager at M.S. Video and DVD, Montague’s last remaining video-rental store, who declined to give his last name. “I’d expect to see the restaurants busy. Everyone’s home, or they’re in Manhattan, or they’re somewhere south of Atlantic Avenue.”

“The thing I miss the most—I would say the biggest change in all of my time on Montague Street, which is approaching 20 years—is the tragic end of the nightlife on Montague Street,” said Mitch Cutler, owner of St. Marks Comics, which has occupied two different addresses along the corridor.

“It used to be full of interesting bars and restaurants,” said Mr. Cutler, who fondly recalled watching the New York Mets clinch the National League Eastern Division pennant against the Chicago Cubs in 1986 at the old Montague Street Saloon. (“The house bought everybody a round,” he said.)

Today, the former saloon has been replaced by a high-end Housing Works thrift shop offering Gucci- and Prada-made goods, with proceeds going to charity. The store closes no later than 7 p.m.

The Irish pub Eamonn’s, which opened in the mid-90’s, is the only true tavern left on the entire strip. Yet its location, surrounded by the cluster of banks between Clinton and Court streets, lends little in the way of retail synergy to businesses farther down the street.

The lack of late-night foot traffic in recent years eventually prompted Mr. Cutler to start sending his comics-shop staff home much earlier.

“When we first started there, we had much later hours, because there were people in the bars all night,” he said. “We were making money all the way up until 11 o’clock. But when there’s no bars, there’s no nightlife, there’s no foot traffic; there’s nobody to buy comics, either. So we shortened our hours.”

Last call for comics is now 9 p.m. at the latest (or as early as 7 p.m. on some nights).

OF COURSE, NOT EVERYONE LIKELY AGREES with Mr. Cutler’s take on the impact of Montague’s nightlife gap. New taverns certainly aren’t included on the family-friendly Brooklyn Heights Association’s Internet-posted wish list of preferred uses for promoting a “more vibrant and balanced” retail scene on Montague Street; kiddies and teen-interest stores are.

“A bar maybe isn’t your first choice, but it draws people to the street,” agreed the association’s Ms. Stanton, who noted that once-beloved Annie’s Blue Moon tavern is now a Prudential Douglas Elliman office. “It’s sad to see how dark Montague Street is at night.”

Ms. Stanton said that her organization is presently lobbying city officials in the hopes of enacting tax incentives or zoning changes to counter the chronic loss of locally owned businesses on Montague and to avoid more banks, real-estate agencies and national chains. (“If we wanted the sameness of malls, we’d move to the suburbs,” mused the so-called First Suburb’s organization newsletter last fall, however ironically.)

Naturally, from a realtor’s perspective, things couldn’t be rosier along the brand-name-logo’d historic strip.

“I don’t think Montague Street has softened up in any way, shape or form,” said Brian Leary, Massey Knakal’s resident downtown Brooklyn expert. “Montague Street will always attract the large nationals and the triple-A tenants.”

And as for those bush-league local shops—well, they can join the retail resurgence elsewhere.

“Where, 10 years ago, Montague Street and Court Street might have been the only viable options for mom-and-pop shops, there are 10 other alternatives in the neighborhood,” Mr. Leary said. “The northern end of Henry Street is a phenomenal location, with terrific mom-and-pops shops. Court Street, once you cross Atlantic, there’s a ton of mom-and-pops—Smith Street, too.

“My feeling is that, in the neighborhood in general, there’s a lot more opportunities for mom-and-pop shops. Maybe not on this immediate corridor, but within the one-mile radius, there’s a lot more opportunity than there was previously, and a lot more inventory.”

But for how long? “I think,” Ms. Stanton said, “it’s only a matter of time before the rents in Cobble Hill and Smith Street push people out, too.”